Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes
| Autor: | Kuiyong Dong, Kan Wang, Yongming Deng, Lynée A. Massey, Hadi D. Arman, Nicole Greco, Kostiantyn O. Marichev, Michael P. Doyle |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Hydrogen 010405 organic chemistry Azetidine chemistry.chemical_element General Medicine General Chemistry 010402 general chemistry 01 natural sciences Copper Medicinal chemistry Article Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry Ylide Hydrogenolysis Yield (chemistry) |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201909929 |
| Popis: | The all-cis stereoisomers of tetrasubstituted azetidine-2-carboxylic acids and derivatives that possess three chiral centers have been prepared in high yield and stereocontrol from silyl-protected Z-γ-substituted enoldiazoacetates and imido-sulfur ylides by asymmetric [3+1]-cycloaddition using chiral sabox copper(I) catalysis followed by Pd/C catalytic hydrogenation. Hydrogenation of the chiral p-methoxybenzyl azetine-2-carboxylates occurs with both hydrogen addition to the C=C bond and hydrogenolysis of the ester. |
| Databáze: | OpenAIRE |
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